MW 473.4 Da, Purity >98%. Novel, selective, cell membrane permeable clathrin inhibitor. Competitively inhibits clathrin terminal domain to selectively inhibit clathrin mediated endocytosis (CME) (IC50 = 12 μM for inhibition of amphiphysin association of clathrin TD). Interferes with receptor mediated endocytosis (RME), entry of HIV and synaptic vesicle recycling.
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- Science advances 9:eadi87162023Anionic nanoplastic contaminants promote Parkinson's disease-associated α-synuclein aggregation.Applications:Unspecified applicationReactive species:Unspecified reactive speciesZhiyong Liu,Arpine Sokratian,Addison M Duda,Enquan Xu,Christina Stanhope,Amber Fu,Samuel Strader,Huizhong Li,Yuan Yuan,Benjamin G Bobay,Joana Sipe,Ketty Bai,Iben Lundgaard,Na Liu,Belinda Hernandez,Catherine Bowes Rickman,Sara E Miller,Andrew B WestPubMed 37976362
- Journal of virology 97:e00770232023Efficient clathrin-mediated entry of enteric adenoviruses in human duodenal cells.Applications:Unspecified applicationReactive species:Unspecified reactive speciesMiriam Becker,Dario Valter Conca,Noemi Dorma,Nitesh Mistry,Elin Hahlin,Lars Frängsmyr,Marta Bally,Niklas Arnberg,Gisa GeroldPubMed 37823645
- Nature communications 14:60152023FEAST: A flow cytometry-based toolkit for interrogating microglial engulfment of synaptic and myelin proteins.Applications:Unspecified applicationReactive species:Unspecified reactive speciesLasse Dissing-Olesen,Alec J Walker,Qian Feng,Helena J Barr,Alicia C Walker,Lili Xie,Daniel K Wilton,Indrani Das,Larry I Benowitz,Beth StevensPubMed 37758703
- Archives of Razi Institute 78:427-4342023The Role of Akt/Rab5A Signalling in Regulating Cell Migration of MDA-MB-231 Breast Cancer Cell Line.Applications:Unspecified applicationReactive species:Unspecified reactive speciesM Chayan,D Al-Fahad,M Al-BedhawiPubMed 37312730
- International journal of molecular sciences 24:2023The Antimicrobial Peptide Cathelicidin Exerts Immunomodulatory Effects via Scavenger Receptors.Applications:Unspecified applicationReactive species:Unspecified reactive speciesRyo Amagai,Toshiya Takahashi,Hitoshi Terui,Taku Fujimura,Kenshi Yamasaki,Setsuya Aiba,Yoshihide AsanoPubMed 36614313
- Frontiers in cell and developmental biology 10:10753642022Mapping of Tilapia Lake Virus entry pathways with inhibitors reveals dependence on dynamin activity and cholesterol but not endosomal acidification.Applications:Unspecified applicationReactive species:Unspecified reactive speciesReem Abu Rass,Japhette Esther Kembou-Ringert,Rachel Zamostiano,Avi Eldar,Marcelo Ehrlich,Eran BacharachPubMed 36605723
- Nature 612:328-3372022PLD3 affects axonal spheroids and network defects in Alzheimer's disease.Applications:Unspecified applicationReactive species:Unspecified reactive speciesPeng Yuan,Mengyang Zhang,Lei Tong,Thomas M Morse,Robert A McDougal,Hui Ding,Diane Chan,Yifei Cai,Jaime GrutzendlerPubMed 36450991
- Neurobiology of pain (Cambridge, Mass.) 12:1001092022Cell specific regulation of NaV1.7 activity and trafficking in rat nodose ganglia neurons.Applications:Unspecified applicationReactive species:Unspecified reactive speciesSantiago I Loya-López,Paz Duran,Dongzhi Ran,Aida Calderon-Rivera,Kimberly Gomez,Aubin Moutal,Rajesh KhannaPubMed 36531612
- Microbiology spectrum 10:e01097222022Human Adenovirus Type 26 Infection Mediated by αvβ3 Integrin Is Caveolin-1-Dependent.Applications:Unspecified applicationReactive species:Unspecified reactive speciesDavor Nestić,Jerome Custers,Danijel Švec,Dragomira MajhenPubMed 35924932
- Frontiers in oncology 12:8356032022Ubiquitin ligase RNF125 targets PD-L1 for ubiquitination and degradation.Applications:Unspecified applicationReactive species:Unspecified reactive speciesMeng Wei,Yunhai Mo,Jialong Liu,Jingtong Zhai,Huilong Li,Yixin Xu,Yumeng Peng,Zhihong Tang,Tao Wei,Xiaopan Yang,Linfei Huang,Xiao Shao,Jingfei Li,Li Zhou,Hui Zhong,Congwen Wei,Qiaosheng Xie,Min Min,Feixiang WuPubMed 35965501
Key facts
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 473.4 Da
- Molecular formula
- C20H13BrN2O3S2
- PubChem identifier
- 137254289
- Nature
- Synthetic
Target data
Recommended products
MW 473.4 Da, Purity >98%. Novel, selective, cell membrane permeable clathrin inhibitor. Competitively inhibits clathrin terminal domain to selectively inhibit clathrin mediated endocytosis (CME) (IC50 = 12 μM for inhibition of amphiphysin association of clathrin TD). Interferes with receptor mediated endocytosis (RME), entry of HIV and synaptic vesicle recycling.
Key facts
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 473.4 Da
- Molecular formula
- C20H13BrN2O3S2
- PubChem identifier
- 137254289
- Nature
- Synthetic
- Solubility
Soluble in DMSO. Please refer to the Protocol Booklet for more information.
- Biochemical name
- 2-(1-Naphthylsulfonylamino)-5-[(Z)-4-bromobenzylidene]-2-thiazoline-4-one
- Biological description
Novel, selective, cell membrane permeable clathrin inhibitor. Competitively inhibits clathrin terminal domain to selectively inhibit clathrin mediated endocytosis (CME) (IC50 = 12 μM for inhibition of amphiphysin association of clathrin TD). Interferes with receptor mediated endocytosis (RME), entry of HIV and synaptic vesicle recycling.
- Canonical SMILES
- C1=CC=C2C(=C1)C=CC=C2S(=O)(=O)N=C3NC(=O)C(=CC4=CC=C(C=C4)Br)S3
- Isomeric SMILES
- C1=CC=C2C(=C1)C=CC=C2S(=O)(=O)N=C3NC(=O)/C(=C/C4=CC=C(C=C4)Br)/S3
- InChI
- InChI=1S/C20H13BrN2O3S2/c21-15-10-8-13(9-11-15)12-17-19(24)22-20(27-17)23-28(25,26)18-7-3-5-14-4-1-2-6-16(14)18/h1-12H,(H,22,23,24)/b17-12-
- InChIKey
- CGDLWHGPJPVPDU-ATVHPVEESA-N
- IUPAC name
- N-[(5Z)-5-[(4-bromophenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]naphthalene-1-sulfonamide
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- +4°C
- Appropriate long-term storage conditions
- +4°C
- Storage information
- Store under desiccating conditions, The product can be stored for up to 12 months
Notes
High concentrations of Pitstop 2™ may interfere with fluorescence imaging due to a low emittance of the compound in the green channel. This fluorescence is not usually detectable if the cells have been first fixed and washed prior to imaging.
Sold under exclusive licence from Children's Medical Research Institute and Newcastle Innovation Ltd. Pitstop® is a trademark of Freie Universitat Berlin, Newcastle Innovation Ltd. and Children's Medical Research Institute.
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3 product images
Chemical Structure - Pitstop® 2, Novel cell-permeable clathrin inhibitor (ab120687)
2D chemical structure image of ab120687, Pitstop® 2, Novel cell-permeable clathrin inhibitor
Dutta D et al. PLoS One. 2012; 7(9): e45799. doi: 10.1371/journal.pone.0045799 Reproduced under the Creative Commons license https://creativecommons.org/publicdomain/zero/1.0/Functional Studies - Pitstop® 2, Novel cell-permeable clathrin inhibitor (ab120687)
Hela cells were preincubated with DMSO (0.1%) or different doses of pitstop 2 (ab120687) ranging from 5 μM to 30 μM. Cells were then allowed to internalize Alexa594-Transferrin and antibodies to MHCI in the presence or absence of the drug for 30 min. After internalization, surface antibody was removed by low pH acid wash. Cells were then labeled with secondary antibodies to detect trasnferrin and MHCI.
Credit: Dutta D et al. PLoS One. 2012; 7(9): e45799. doi: 10.1371/journal.pone.0045799
Von Kleist L et al., Cell. 2011 Aug 5;146(3):471-84. Fig, 3(A-E)., doi: 10.1016/j.cell.2011.06.025.Functional Studies - Pitstop® 2, Novel cell-permeable clathrin inhibitor (ab120687)
A) Pitstop® 2 reversibly inhibits Tf uptake. After 15 min preincubation HeLa cells were incubated with Alexa Fluor® 568-Tf in the presence of DMSO or 30 µM Pitstop 2 for 15 min. Tf uptake is seen to resume after washout of the drug for 1 hr. Scale bar, 10 mm. B) Reversibility and dose dependence of Pitstop® 2-mediated inhibition of Tf uptake. Data represent SEM (n = 3 independent experiments; *p < 0.05, ***p < 0.0001). C) Pitstop® 2 inhibits EGF uptake. HeLa cells pretreated with 30 µM pitstop 2 or DMSO for 15 min were incubated for 15 min with Alexa Fluor® 488-EGF in the continued presence of inhibitor. Data represent SEM (n = 3 independent experiments; ***p < 0.0001). D) Pitstop 2 does not interfere with AP-2-mediated cargo sequestration into CCPs. TIRF microscopy images of Cos7 cells pretreated with DMSO or 30 µM Pitstop 2 for 15 min were incubated with Alexa Fluor® 488-EGF at 8oC in the continued presence of inhibitor and immunostained for AP-2a (red). Scale bar, 4 mm. E) Pearson’s
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